4-fluorophenanthridin-6(5H)-one | 1238333-89-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-fluorophenanthridin-6(5H)-one
• 英文别名: 4-fluoro-5H-phenanthridin-6-one
• CAS: 1238333-89-5
• 化学式: C₁₃H₈FNO
• 分子量: 213.211
• InChiKey: SYEXEJOQTMTFQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-fluorophenanthridin-6(5H)-one 在 三氯氧磷 作用下， 生成 4-fluorophenanthridine
  参考文献：
  名称：

  Design of fluorinated 5-HT4R antagonists: Influence of the basicity and lipophilicity toward the 5-HT4R binding affinities

  摘要：

  Analogues of potent 5-HT4R antagonists possessing a fluorinated N-alkyl chain have been synthesized in order to investigate the effect of the resulting change in basicity and lipophilicity on the affinity and selectivity profile. We demonstrate that for this series, the affinity is decreased with decreased basicity of the piperidine's nitrogen atom. In contrast, the resulting increase in lipophilicity has minimal impact on binding affinity and selectivity. 3,3,3-Trifluoropropyl and 4,4,4-trifluorobutyl derivatives 6d and 6e have shown to bind to the 5-HT4R while maintaining their pharmacological profile and selectivity toward other 5-HT receptors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.061
• 作为产物：
  描述：

  2',3'-difluorobiphenyl-2-carbonitrile 在 potassium hydroxide 、 盐酸 作用下， 以 叔丁醇 、 水 为溶剂， 反应 0.5h， 以90%的产率得到4-fluorophenanthridin-6(5H)-one
  参考文献：
  名称：

  General method for the synthesis of substituted phenanthridin-6(5H)-ones using a KOH-mediated anionic ring closure as the key step

  摘要：

  Substituted phenanthridin-6(5H)-ones were obtained in a two-step procedure involving a Suzuki cross-coupling reaction followed by a KOH-mediated anionic ring closure. The influence of the nature and the position of the substituents on the cyclization step were studied. This methodology offers a general and practical route to diversely substituted phenanthridin-6(5H)-ones. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.014

文献信息

• Synthesis and Structure–Affinity Relationships of Selective High-Affinity 5-HT₄ Receptor Antagonists: Application to the Design of New Potential Single Photon Emission Computed Tomography Tracers
  作者：Emmanuelle Dubost、Noé Dumas、Christine Fossey、Rosa Magnelli、Sabrina Butt-Gueulle、Céline Ballandonne、Daniel H. Caignard、Fabienne Dulin、Jana Sopkova de-Oliveira Santos、Philippe Millet、Yves Charnay、Sylvain Rault、Thomas Cailly、Frederic Fabis

  DOI：10.1021/jm300943r

  日期：2012.11.26

  The work described herein aims at finding new potential ligands for the brain imaging of 5-HT4 receptors (5-HT4Rs) using single-photon emission computed tomography (SPECT). Starting from the nonsubstituted phenanthridine compound 4a, exhibiting a Ki value of 51 nM on the 5-HT4R, we explored the structure–affinity in this series. We found that substitution in position 4 of the tricycle with a fluorine

  本文描述的工作旨在寻找新的潜在配体，用于使用单光子发射计算机断层扫描 (SPECT)对 5-HT 4受体 (5-HT 4 Rs) 进行脑成像。从未取代的菲啶化合物4a 开始，在 5-HT 4 R上表现出51 nM的K i值，我们探索了该系列中的结构-亲和力。我们发现用氟原子取代三环的 4 位得到了最好的结果。在三环骨架内引入额外的氮原子导致对 5-HT 4 R的亲和力和选择性增加，表明拮抗剂4v的设计，表现出 0.04 nM 的高亲和力。然后合成了几种碘化类似物作为潜在的 SPECT 示踪剂。碘化化合物11d能够取代参考放射性碘化 5-HT 4 R 拮抗剂（1-丁基哌啶-4-基）甲基-8-氨基-7-碘[ 123 I]-2,3-二氢苯并[ b ][1 ,4]dioxine-5-carboxylate [ 123 I] 1 , [ 123 I]SB 207710} 体外和脑内。化合物11d用
• KO^<i>t</i>Bu Mediated Synthesis of Phenanthridinones and Dibenzoazepinones
  作者：Bhagat Singh Bhakuni、Amit Kumar、Shah Jaimin Balkrishna、Javeed Ahmed Sheikh、Sanjit Konar、Sangit Kumar

  DOI：10.1021/ol301077y

  日期：2012.6.1

  Synthesis of substituted phenanthridinones and dibenzoazepinones has been realized from 2-halo-benzamides in the presence of potassium tert-butoxide and a catalytic amount of 1,10-phenanthroline or AIBN. This new carbon–carbon bond forming reaction gives direct access to various biaryl lactams containing six- and seven-membered rings chemoselectively. Carbon–carbon coupling seems to proceed by the generation

  在叔丁醇钾和催化量的1,10-菲咯啉或AIBN的存在下，由2-卤代苯甲酰胺合成了取代的菲啶酮和二苯并a庚酮。这种新的碳-碳键形成反应可直接接近具有化学选择性的六元和七元环的各种联芳基内酰胺。碳-碳偶合似乎是通过酰胺环中自由基的产生而进行的，从而导致苯胺的CH芳基化。